issuing goods to courier to execute the delivery to customer

Hi Experts :)

Case: the company does not execute the delivery, they issue the goods to a delivery agent which is out-sourced, and the courier handles the delivery based on a contract with the issuing company and the courier company.

in this case;

1- should there be an outbound delivery document for the sales order?

2- what integration needs to be done between SD and WM if the issuing warehouse is WM managed?

As of now, regular MM is configured but i will need the integration between WM and SD.

Please advice.

Thank you in advance

AH